How To Plan Your Next WorkCation

I love workcation’s because they galvanize my creative potential, heighten my productivity and they’re incredibly recharging.

When I am not recording music, voiceovers or editing huge blocks of footage in my studio, I’m either on a workcation or I’m planning the next one.

The premise behind a workcation is to blend pleasure and fun by traveling all over the world without taking a break from work.  As long as you’re an entrepreneur that has work that can be accessed and completed via computer, you’re a candidate for a workcation.

Yes, you can actually get shit done while traveling the world. Can you imagine writing your next novel or ebook on a granite table while overlooking luminous blue seas and sherbet skies in Phuket? What about your next TV script? What if you could write that on a bench in a rain forest? Sounds absolutely magical and even better — it’s absolutely possible.

Today, I am going to share with you how you can make your workspace mobile.

I love workcation’s because they allow me to complete large concentrated amounts of work in short sprints. By setting blocks of time specifically dedicated to completing specific tasks, I find I can easily knock out the most mundane tasks calling for my attention as well as tasks (like editing or marketing) that require large dedicated amount of time sitting in one spot at the corner of the couch. But instead of doing it with the view of my backyard, I’d rather look ahead to an infinity pool.

How To Plan Your Next Workcation:

Step 1 – Choose Your Destination

First, decide if your adventure will be local or if you will you choose an exotic destination?

Working vacations can either be 3-4 days if local or 5-10 days if traveling long distance. For me, my average workcation including travel is 4 days.

Workcation | High-Rise Views - Miami Condo
High-Rise Views – Miami Condo

You can always stay longer but keep in mind staying longer could mean more play and less work.

The goal is to increase productivity while having fun but you don’t want to fall off your routine.

How to choose the best Workcation length? Make a list of things that would cause your business to suffer if you went away too long.

For me, this would be disappearing to Europe for a month long trip. I simply spend a lot of time in recording studios and rarely have time to step away longer than 3-4 days. A week I could get away with , but two weeks would definitely be pushing it. Four weeks, and you might as well have told everyone in the entertainment / music industry that I quit. In an industry where opportunity derives from 99% of the relationship you make, stepping away from relationships that long may not be a good idea.

Second, where will you stay?

Some love hotels, others like private residences. I love hotels but I really love private residences. I love the convenience of parking, the exclusiveness and I love how it gives you that home away from home feel. Hotels can feel like this as well if you stay somewhere in a villa.

But then again, places like Airbnb tend to be a fraction of the price of a hotel. Through Airbnb, sometimes you can find non-scammy deals for a 5-star quality experience at the price of a 3-star hotel.

Step 2 – Find Wi-Fi

When I am traveling within the U.S, I don’t worry about Wi-Fi so much because I use my iPad as a hot spot. Plus, Wi-Fi is a pretty standard feature to have here. But when you’re traveling to some place like Mexico or Europe, this gets expensive. Research ahead of time if the hotel or private residence your staying at has Wi-Fi.

You can also ask the place you’re staying at to send you a screenshot from speedtest.

Step 3 – Automate Your Business

Whenever I travel, I try to automate 90% of my work. That includes writing and planning blogs ahead of time and scheduling social media posts. Most of you probably already know how to do this but here is a trick I’ve learned.

 Workcation | Miami
High-Rise Views from Condo – Miami

I don’t just plan the days that I travel, but I also plan and automate posts and / or social media up to  3 days after I return. Why?

Whenever I return home (especially after long flights),  I am extremely exhausted and worn out for 24-48 hours after I land. These are the times I need a break most and I find the fastest way for me to recover is to allow myself to actually recover.

This is because sometimes my workcation’s can include some hardcore labor such as carrying film equipment, going to studios, setting up for festivals and etc.

Whenever I try to power through after I return home, it works for about 4 days and then I pretty much just crash. As you know, when you incur burnout, this can throw you off for another week. Yikes!

Also, sometimes I’m just inundated with random emails and spend quite of time catching up. My mind is so fogged and the last thing I want to worry about are social media posts.

Step 4 –  Consider Taking the Trip with Your Business Bestie or Alone

First, consider if your work calls for traveling alone or with others.

If I go on a working vacay due to a creative drought, I like to go alone. As an introvert, alone is how I recharge best and is most optimal for me unless working on a collaborative project.

On the other hand, if I go on a working vacation and all I have is administrative work like registering a gazillion songs on ASCAP, editing tons of footage or revisiting a marketing plan, I don’t mind kickin’ it with others. Its even more fun traveling with others if you’re working on a collaborative project. But if you haven’t already seen where this is going, I’ve mentioned nothing about going on a working vacation with friends.

As much as I try to set boundaries when I travel with friends, I’ve learned that some friends you can workcation with but most simply won’t understand your working vacay. To them, it’s work or vacation and you can’t have both. Hence, why they’re normal and you’re an entrepreneur.

Bottom line, first decide what type of social environment you need to succeed. And if you do decide to travel with others, consider only workcationing with your business bestie’s or friend’s that are entrepreneurs.

5 – Set Realistic Expectations and Goals.

A successful workcation is more than just about choosing a destination and bringing your laptop. Before you get in your car or step on that plane, set realistic work expectations and goals.

For me a realistic goal involves outlining my priority task and which days each task will be assigned to. And then creating blocks of time that I allow myself to complete each tasks, and blocks of time dedicated towards fun.

 Workcation | On Set Filming For Lilumia + Secret TV Project
On Set Filming For Lilumia + Secret TV Project in Miami | Yes, I’m the director! 😉

BEHIND THE SCENES: You don’t have to travel far to have a great Workcation. Currently I live in Atlanta and just last week I took a workcation in Miami. Sometimes I just like to drive three hours away, and other times my friends and I pick a destination in the US to work on fun projects. While traveling outside of the country is so much fun, you can still have a great time even if you just drive to the next city.

Step 6 – Block Out Work Times

Depending on the task, I will either reserve portions of my day, usually mornings (9am-12pm) where I complete one priority task.

Normally these tasks are big like filming for a TV project, setting time for editing and etc.

But as someone who enjoys the thrill of a good sprint, if I plan a workcation, sometimes I’ll reserve two days dedicated to cramming in as much work as possible. This isn’t ideal for everyone, but when a girl gets her groove, she is not letting off anytime soon.

Step 7 – Pick One Project and Limit the Tasks You take on

Whatever you do, make sure you’re not overwhelming yourself with a long to-do list. As I said before, prioritize tasks. A lot of times when I workcation, I am working on one project. For example, if I am filming content for television, I pick blocks of time to film and blocks of time to edit. But I am working on one project and spreading it across my week.

Step 8 – Plan Fun Activities Ahead of Time

Before I workcation, I try to plan all activities and sightseeing ahead of time. I usually reserve mornings for work and 1 – 7pm for fun.

This is why I also love living social and groupon. You can totally take advantage of purchasing fun activities well ahead of time and for a discounted price.



Join thousands of monthly insiders and get access to my library
of free resources for Creative Entrepreneurs.